From Wall Street To NYC Cabbie: What I Learned On The Way Down

"Let's take a look at your numbers." It was only days after 9/11, when he'd narrowly escaped his World Trade Center office, and this comment from his manager made Jack Alvo snap. He quit his six-figure job at Morgan Stanley and began a decade-long career path that would end in an unlikely spot: As a New York cabbie.

Alvo, 50, who spent years working in finance, earning as much as $250,000-a-year, never expected to drive a cab. But it's brought some unexpected joys. He says that he doesn't envy the finance guys whom he drives around all day, six days a week, from 5 a.m. to 5 p.m. In fact, it's given the cabbie a new outlook. "I don't want to go back to that lifestyle," of working on Wall Street, he says. "It's grueling, grueling."

Looking back, the cab driver's career really changed the morning of 9/11, when Alvo escaped from his 73rd floor office of the South Tower. Fresh from this trauma, Alvo says that couldn't handle the single-minded profit focus of certain Morgan Stanley managers. He did a couple other jobs, in commercial real estate and metal trading, but was laid off in 2009.

In the midst of the financial crisis, he bumped around for a year, unable to find work, scraping by with his wife and two kids in their rent-stabilized apartment. So he decided to start driving a cab. "I needed to bring in cash," he said, and he knew the city streets well.

The same skills apply

Alvo says that he turned out to be a great cabbie. His aptitude for figures, honed through years of financial trading, worked well in a job where time is truly money. "I break it down literally to -- I'm a numbers guy -- to every 15 minutes," he said. By 7 o'clock in the morning, he claims that he can predict his end-of-day income. "I'll usually be within $20," he adds.

Alvo's many years as a taxi passenger also helps him relate to his clientele. When finance guys jump in the back, they're often surprised how well-versed their driver is in the fits and starts of the bond market.

"It's fishing," he said about his new career. "If you don't know what you're doing, you'll never catch a fish. But if you know what you're doing, you'll have dinner every night."

Driving a cab might not seem like it provides much opportunity for innovation. But Alvo says that he has always been an entrepreneur in spirit, and since around 200 people a week took a ride in his car, the chances were that at least someone, he thought, if they knew his credentials, would have a job lead. So Alvo installed a magazine rack in the back of the car, and placed his resume on it, along with the sign: "Driver's resume: If you have someone who can help in your network, I'm all ears."

The offers started coming: something in fashion, in health care, in networking marketing. "In my '20s or '30s I would have jumped at those positions pretty quickly," he said. But "as time went on, I wasn't so motivated to just jump at anything."

Alvo also had interviews with major financial firms like Citigroup and Bank of America. He says that he finally got close to his years-long goal of returning to finance, and its six-figure salary. But yet, he just couldn't get excited about any of it. "I'm growing out of it," he thought.

Alvo is no longer looking for just a job; he wants a completely new career. "You have to be completely creative, think outside the box," he said about unemployed or underemployed people like himself. Right now, Alvo's interested in helping a startup develop, writing a book, and possibly pitching a TV show. (He says that he's already turned down a reality TV offer.)

And until he finds the right fit, Alvo's happy to go on savoring the freedom of his current life, driving the streets of New York, blasting opera, and meeting dozens of different people a day. Yes, his family has settled into a life with less -- no dinners out, no elaborate vacations -- and he works 12-hour shifts, six days a week.

"It's a constant and consistent hustle," he says of the cabbie lifestyle. "You start off $200 in the hole everyday, and you gotta make up that and your own income."

But somehow, the whole ordeal has brought his family a little closer, he says. It's also given him a zen-like attitude to life: the knocks it can throw at you, and the possibilities.

"Why is a guy with this kind of resume also behind the wheel of a taxi?" a guy recently asked him. Alvo wasn't offended. He didn't feel the need to explain. "A young guy doesn't get it," said Alvo. "An old guy gets it."